I was thinking about this at work today. Suppose the Imperials would take over Windhelm, would they threat the Dunmer and in particular the Gray area in Windhelm, better than there predecessor Ulfric Stormcloak? I'm questioning this, because with my current character I'm still uncertain which side to choose, so i'm weighting different point of views and factors concerning the Stormcloaks and Imperials.

Well. I enjoyed the peace and quiet...

Should the Legion take over Windhelm, Free-Winter states that he's already been in the works on improving their condition (I never see this), but that the Nords are rock headed, stubborn, and slow to change. The Dunmer and Argonians however, seem happy that the Stormcloaks and their prejudice is gone.

There is only one way to find out......join the legions

That is more so on Bethesda in the first place for not much change taking place.

The only significant changes done are a swap in the guards, a couple angry Nords and some happy Dunmer and Argonians.

The real question is why are the Windhelm Dunmer doing so poorly when Altmer citizens of Windhelm all own businesses and are doing very well economically and are allowed to live in the upper quarter with their Nord counterparts.

You ought to consider the fact that the N'wah Quarter had been a slum long before Ulfric was even born.

If the Empire did not care about it then, I doubt that they would care about it now.

Don't forget about the Cyrods.

Also, go to the second floor of the New Gnisis cornerclub for a very interesting sight.

Aaaaaaannnd cue the extremely lengthy argument that will more than likely get pretty heated

I think...

The situation is Windhelm is what happens everywhere when a lot of refugees of the same culture come to a new country, and this country isn't doing particularly well either, although way better than where the immigrants came from.

Considering the climate (and upbacked by in-game dialogue) it seems Windhelm would have some problems with poverty even without the Dunmer immigrants. Ant the civil war makes it worse. UIfric is annoyed with the Dunmer because he needs all his resources in the civil war, but it would be a smart move of him to win them over! The majority of the Dunmer don't like the Empire. OTOH Ambarys Rendar seems to be an important figure in the Gray Quarter, and his influence might be a problem here.

If the Imperials win the war, they might be interested in scoring political points by doing something for the Dunmer and trying to do something about the racial conflicts in the city. So if they're smart, yes, they will at least try to improve the situation.

If the Stowmcloaks win, Ulfric will probably put most energy into rebuilding the destroyed cities, so it could take a while before he does something about his own city.

*edited for typos

In my opinion it isn't the Empire's place to treat the Dunmer better than the Stormcloaks. It's way too micro of a thing for them to deal with.

Consider this. The Empire is more of a federal government, operating on a national level, and based in Cyrodiil. The Dunmer problem is in Skyrim. Moreover, it isn't a problem manifesting throughout the entire province, and is focused in Eastmarch. Beyond that, it's isolated to Windhelm, a single city in the Hold.

It's a local matter, and should be handled by the local government, not the federal government. In this case, the Jarl of Eastmarch.

That said, the Jarl who comes to power should the Empire take Windhelm is more sympathetic to their plight than Ulfric.

The Dunmer and Argonians are happy seeing them in power, so yes.

I think the options should be worded better.

Instead of "Yes, Absolutely!" to "More likely".

Of course they would. The Empire even laid special protection rules for the Giants of Skyrim, the Empire would most likely be backing Free-Winter in reconciling with the Dunmer.

Bottom line, the central location in the empire occupied by Cyrodiil would tend to make the population there more familiar with racial mixing than any of the provincial populations would be. So natives of Cyrodiil would tend to be more tolerant. But the problems in Windhelm aren't 'due to the Jarl', they're in the nature of the provincial population and amplified by the harsh conditions. Imperial governance isn't going to change that...at least for a number of generations.